Dimethylformamide → HCID 875976, compound

HRID 1686453Notes

Reaction equation

HRID 1686453 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:13](Cl)(=O)[C:14](Cl)=O.[CH3:19][N:20]([CH:22]=O)C>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([N:20]1[CH2:22][CH2:14][CH2:13][CH2:19]1)=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 7371712-Chloro-4,5-difluorobenzoic acid

Product 1

HCID 875976HCID 875976, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-chloro-4,5-difluorobenzoic acid (1.0 g) in DCM (10 ml) was treated with oxalyl chloride (0.45 ml) followed by a drop of DMF. The mixture was stirred at RT for 1 h before evaporating under reduced pressure. The solid was dissolved in DCM (20 ml) and pyrrolidine (2 ml) was added and stirred at RT overnight. The mixture was diluted with water, extracted with DCM, dried (MgSO4) and evaporated under reduced pressure to give an oil (1.45 g).

Workup

  1. custombefore evaporating under reduced pressure
  2. dissolutionThe solid was dissolved in DCM (20 ml)
  3. additionpyrrolidine (2 ml) was added
  4. stirringstirred at RT overnight
  5. additionThe mixture was diluted with water
  6. extractionextracted with DCM
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7eef5601c9c147dc8224ada9eaa71561
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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